Huperserratines A and B, Two Macrocyclic Lycopodium Alkaloids with an Unusual Skeleton from Huperzia serrata

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Abstract
Huperserratines A (1) and B (2), two Lycopodium alkaloids with an unprecedented 5-aza-bicyclo[10.4.0]hexadecane skeleton and an oxime function, were isolated from Huperzia serrata. Their structures including absolute configurations were determined by extensive NMR spectroscopic and X-ray diffraction analysis. Compounds 1 and 2 were the first examples of macrocyclic Lycopodium alkaloids with a aza-12-membered ring. Plausible biogenetic pathway of these compounds was also proposed. Compound 1 exhibited moderate anti-HIV-1 activity with EC50 of 52.91 gmL and therapy index more than 3.78.
Funding Information
  • Youth Innovation Promotion Association of the Chinese Academy of Sciences
  • State Key Laboratory of Phytochemistry and Plant Resources in West China (P2017-KF13)
  • National Natural Science Foundation of China (21837003)
  • Yunnan Province

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